


Stuck in the Middle

by TheLittleRedWhoCouldWrite



Series: Color [4]
Category: Supernatural
Genre: Alternate Universe - Smith/Wesson, Anal Fingering, Anal Sex, Dominant Reader, Dominant Sam, Female!Reader - Freeform, Light Bondage, Multi, Pegging, Reader-Insert, Strap-Ons, Submissive Dean, Threesome - F/M/M, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2015-12-20
Updated: 2015-12-20
Packaged: 2018-05-07 21:23:04
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,089
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5471249
Author URL: https://archiveofourown.org/users/TheLittleRedWhoCouldWrite/pseuds/TheLittleRedWhoCouldWrite
Summary: <blockquote class="userstuff">
              <p>“How do you want him?” Sam asks, big hands sliding up and down Dean’s arms.</p><p>“On the bed, on his knees.”</p><p>You take the strap-on harness from its hook and fit the dildo into its spot.</p><p>--</p><p>In which our trio tries pegging.</p>
            </blockquote>





	Stuck in the Middle

You open the cupboard and eye the contents. A series of dildos in various shapes and sizes line the shelves. So many options. You turn to Dean.

The sub is kneeling on the floor, naked with his hands bound behind his back. Sam is standing over him, arms folded across his bare chest. He, too, is naked.

“Would you like to choose, pet?” you ask.

“If it pleases you, Mistress,” Dean replies obediently.

You beckon and Sam helps Dean stand. The older man’s eyes go wide when he sees the choices laid before him.

“The… the purple one,” he says after a long moment of consideration.

“This one?” you pluck the toy in question from its spot. It’s about ten inches long, just a little smaller than Sam himself, and ridged all along it's length.

“Yes, Mistress,” he says, nodding.

You press a soft kiss to his lips. “Good boy.”

A shiver of pleasure runs through him at the praise.

“How do you want him?” Sam asks, big hands sliding up and down Dean’s arms.

“On the bed, on his knees.”

You take the strap-on harness from its hook and fit the dildo into its spot. Dean goes to the bed, where Sam helps him up onto his knees. He falls forward onto his shoulders, ass presented.

“What’s your color?” Sam asks, running a hand along Dean’s spine.

“Green, sir,” Dean answers.

“Alright.”

You tighten the last strap around your waist and move to stand at the foot of the bed. “Spread your legs a little, pet.” He obeys and you climb up onto the bed. Sam passes you the bottle of lube. You spread some on your fingers and begin working open the furled muscle of Dean’s hole. “Stay still.”

Dean whines, but doesn’t move. Slowly, but surely, his hole loosens to allow three fingers, and then finally four, in.

You pull your fingers out, ignoring Dean’s small noise of protest, and slick up the toy. You press the tip to his hole and push in.

Dean gasps. His limbs tremble with the effort to stay still as you guide the dildo deeper. The ridges rub over his insides, catching every pleasure point. You know you’ve hit his prostate when he gives a loud cry and his back arches, thrusting his ass back onto the intrusion.

“Hey,” you say, even as Sam reaches around to deliver a firm smack to each ass cheek. “Hold still, pet.”

“’m sorry, Mistress,” he moans, fists clenching and unclenching as you work your way deeper.

“Apology accepted,” you assure him, rubbing a hand in the small of his back.

“Thank you, Mistress.”

You bottom out, hips colliding with Dean’s ass. You wrap your fingers around his hips and set up a steady rhythm, starting slow and working your way up. You glance over at Sam, who is sitting with spread legs, one hand wrapped around his cock. He’s eyeing you hungrily. You grin and gesture for him to come closer. He does, walking around the bed to stand beside you.

Without breaking rhythm, you reach up and draw your fellow Dominant down into a fierce kiss. He growls and one hand slips between your legs from behind. A long finger slides between the slick folds of your pussy.

“What do you think?” he asks, breath hot on your lips.

“I think there’s a very good reason I love you so much,” you reply.

He grins and plunges his finger into your wet heat. You hum in pleasure and hold still to allow Sam to work, much to Dean’s dismay. He whimpers, but doesn’t complain.

“Patience,” you sooth, leaning forward to give Sam better access. “Let Master work.”

“Yes, ma’am,” the sub responds.

“Good boy.”

Sam works you open quickly, eager to be inside. Once he feels you’re ready, he rolls on a condom and pushes in.

You groan as the huge cock forces you open. You’ll never get used to it, but that’s alright. The feeling of Sam’s length pushing your walls apart, stretching you further than any man ever has, is one of your favorite sensations.

Once he’s settled, you begin moving again. Forward into Dean, back onto Sam. The other Dom quickly grows impatient and begins to move as well. His pace sets your own, driving the dildo deeper. You bend of Dean’s back so you can wrap one arm around his waist. You curl your fingers around his cock.

“Color?” you ask.

“Green!” Dean cries out, struggling to keep still as you fuck him. “Please, Mistress!”

“Please what? Be specific, pet.”

“Please may I come?”

“Yes.”

That one word has Dean spilling hot come over your fingers. His cock twitches in your hand as you milk ever last drop from him. Sam manages to work his hand between you and Dean to rub a finger across your clit, sending your tumbling over the edge. You clench down hard on his cock and he follows you into ecstasy with a loud groan.

You and your boys remain on the bed in a pile of limbs for a while. Then Sam carefully pulls out. You do the same, admiring the way Dean’s hole flutters, grasping at empty air. You untie him and push his arms up over his head, stretching the muscles.

Sam ties off the condom and throws it away. While you take care of Dean, Sam deftly undoes the buckles of your strap-on and removes the harness. He places both parts in the box of dirty toys for Dean to clean tomorrow.

“How’re you feeling?” you ask Dean, helping him roll onto his back and out of his wet spot.

“Good,” he murmurs.

“I’m glad. What do you need?”

“Cuddles?” he says hopefully.

“We can do that. Let’s get you cleaned up and we’ll move to the bedroom.”

Sam wipes you both down with a damp towel, and then passes you a soft blanket. You sit Dean up and wrap him in it. Sam then scoops the smaller man up in his arms, grunting softly. He carries him down the hall to the bedroom, where it’s Dean’s turn to be the middle of the sandwich as you and Sam surround him on the bed. He happily burrows into your embraces, content to let you take care of him.

“I’m guessing pegging is something we’ll be doing again?” you say, flipping through the channels until you find one playing Dr. Sexy.

“Uh-huh,” Dean mumbles against your collarbone. “Lots.”

You exchange a fond smile with Sam. “We’ll keep that in mind.”

**Author's Note:**

> Leave any prompts for scenes you'd like the reader and the boys to play out in the comments.


End file.
